ethyl (8S,11R,14R)-11-[(4-hydroxyphenyl)methyl]-5,18-dimethoxy-14-[(2-methylpropan-2-yl)oxycarbonylamino]-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-8-carboxylate | 143145-51-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (8S,11R,14R)-11-[(4-hydroxyphenyl)methyl]-5,18-dimethoxy-14-[(2-methylpropan-2-yl)oxycarbonylamino]-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-8-carboxylate
• CAS: 143145-51-1
• 化学式: C₃₄H₃₉N₃O₁₀
• 分子量: 649.698
• InChiKey: DJEAYNFNYJFUIJ-ZJGIAAPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  171
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 palladium on activated charcoal lead(IV) acetate 、 盐酸 、 甲醇 、 硫酸 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 1-羟基苯并三唑一水物 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 丙酮 、 乙腈 为溶剂， 反应 110.24h， 生成 ethyl (8S,11R,14R)-11-[(4-hydroxyphenyl)methyl]-5,18-dimethoxy-14-[(2-methylpropan-2-yl)oxycarbonylamino]-10,13-dioxo-2-oxa-9,12-diazatricyclo[13.3.1.13,7]icosa-1(18),3,5,7(20),15(19),16-hexaene-8-carboxylate
  参考文献：
  名称：

  Studies directed toward the synthesis of glycopeptide antibiotic teicoplanin: first synthesis of the N-terminal 14-membered ring

  摘要：

  The N-terminal 14-membered ring formed by an ether linkage between the phenyl moieties of amino acids 1 and 3 of glycopeptide antibiotic teicoplanin 1 plays a crucial role in binding of C-terminal D-Ala-D-Ala residues of the peptidoglycan precursor, thereby inhibiting bacterial cell wall biosynthesis. Herein, the first stereocontrolled synthesis of this very important cyclic peptide 2 is described. The two alpha-arylglycines present in this segment are constructed in optically pure form by diastereoselective Strecker synthesis using alpha-phenylglycinol as chiral auxiliary. Finally, the coupling between the acid function of amino acid 1 and the amino function of amino acid 2 leads to the desired macrocyclization. Optical purity of the synthetic product is determined by NMR studies.

  DOI：

  10.1021/jo00046a031

文献信息

• Studies directed toward the synthesis of glycopeptide antibiotic teicoplanin: first synthesis of the N-terminal 14-membered ring
  作者：T. K. Chakraborty、G. Venkat Reddy

  DOI：10.1021/jo00046a031

  日期：1992.9

  The N-terminal 14-membered ring formed by an ether linkage between the phenyl moieties of amino acids 1 and 3 of glycopeptide antibiotic teicoplanin 1 plays a crucial role in binding of C-terminal D-Ala-D-Ala residues of the peptidoglycan precursor, thereby inhibiting bacterial cell wall biosynthesis. Herein, the first stereocontrolled synthesis of this very important cyclic peptide 2 is described. The two alpha-arylglycines present in this segment are constructed in optically pure form by diastereoselective Strecker synthesis using alpha-phenylglycinol as chiral auxiliary. Finally, the coupling between the acid function of amino acid 1 and the amino function of amino acid 2 leads to the desired macrocyclization. Optical purity of the synthetic product is determined by NMR studies.